S-tert-Butylthio-L-cysteine
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S-tert-Butylthio-L-cysteine

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Category
L-Amino Acids
Catalog number
BAT-004201
CAS number
30044-51-0
Molecular Formula
C7H15NO2S2
Molecular Weight
209.30
S-tert-Butylthio-L-cysteine
IUPAC Name
(2R)-2-amino-3-(tert-butyldisulfanyl)propanoic acid
Synonyms
L-Cys(StBu)-OH; 3-(tert-Butyldithio)-L-alanine
Appearance
White powder
Purity
≥ 99% (TLC)
Density
1.225 g/cm3
Melting Point
177 °C (dec.)
Boiling Point
324.7°C
Storage
Store at 2-8°C
InChI
InChI=1S/C7H15NO2S2/c1-7(2,3)12-11-4-5(8)6(9)10/h5H,4,8H2,1-3H3,(H,9,10)/t5-/m0/s1
InChI Key
TWMBHZTWEDJDRC-YFKPBYRVSA-N
Canonical SMILES
CC(C)(C)SSCC(C(=O)O)N

S-tert-Butylthio-L-cysteine is a derivative of the amino acid cysteine, featuring a tert-butylthio group attached to the sulfur atom. It belongs to a class of compounds known as S-alkylated cysteine derivatives, which exhibit unique structural properties due to the presence of the bulky tert-butylthio side chain. This modification is crucial because it can impact the molecule’s reactivity, solubility, and interactions with biological molecules. S-tert-Butylthio-L-cysteine is primarily synthesized for use in biochemical and pharmaceutical research, where it can play roles in studying enzyme mechanisms, protein modification, or as a building block in drug synthesis.

One of the primary applications of S-tert-Butylthio-L-cysteine is in the field of drug development. In pharmaceutical research, it can serve as a precursor or intermediate in the synthesis of drugs due to its ability to mimic the natural L-cysteine structure while offering additional chemical flexibility. This quality makes it valuable for developing inhibitors or modulators of enzymes that interact with cysteine residues, potentially leading to novel therapeutic agents. Additionally, its modified structure could help enhance the pharmacokinetic properties of drug candidates, including their stability, absorption, and distribution.

In the realm of biochemical research, S-tert-Butylthio-L-cysteine is used extensively to study protein function and enzyme mechanisms. Given its similarity to cysteine, it can be incorporated into peptide chains and used to probe the role of sulfur-containing amino acids in proteins. Researchers employ it to understand disulfide bond formation and cleavage, as well as redox mechanisms that involve cysteine residues. This application extends to designing and testing new protein-based drugs or modifying existing proteins to alter their activity or stability in physiological conditions.

S-tert-Butylthio-L-cysteine also finds uses in agricultural chemistry, particularly in the development of agrochemicals. Its unique structural properties enable the exploration of new formulations for plant protection products or growth regulators. By modifying the sulfur group, agrochemical researchers aim to create compounds that can offer enhanced resistance to pests or environmental stressors, thereby improving crop yields and sustainability. The ability to tailor its chemical structure allows for the fine-tuning of physiological effects and environmental safety of the resulting agrochemical products.

Finally, in material sciences, S-tert-Butylthio-L-cysteine might play a role in developing novel biomaterials. Its functional groups can be exploited to create new polymers or conjugates that have desirable properties for biomedical applications, such as drug delivery systems or scaffolds for tissue engineering. By integrating S-tert-Butylthio-L-cysteine into polymer backbones, researchers can tailor the mechanical properties and biodegradation rates of materials, potentially leading to innovative solutions in medical implants or controlled release technologies.

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